Is it appropriate to confront a higher rank when they are blatantly disregarding regs?

Fuck tact. What happened to having a pair? Ask her if she forgot how she got there? Light her ass up... especially if she is in uniform. Make sure you are on point before you do. CSM O'Black has a great approach, but I would attack with the "Hey Ursula, you got any of that boot polish left? I need a buff on my boots!"

It’s usually not what you say, but how you say it. Although, to be fair, the shade looks like darkish plum, which is actually a good color for that skin tone. Does it meet reg? I don’t know.

There is this thing called on the spot corrections in the Military. It is a very useful tool to address code and reg violations to ANYONE by EVERYONE. There is also a thing called courtesy and tact. First off you should never talk down to anyone while using this tool. It is not there for someone to put themselves on a pedestal while shaming another. It is plain and simple a corrective tool. However if you find yourself in a situation where you find yourself intimidated by a much higher rank and you are shamed for using this tool then that person does not deserve that rank or leadership position. One of the most important things a GOOD leader learns on their way to becoming a good leader is humility. I have taken many on the spot corrections from lower enlisted all the way to a 4 star General's staff. I accept my mistakes gratitude and HUMILITY. Not with scorn and attitude. No one should ever take it personally and if they do then they are weak and petty.

Nothing better to do?

Back when I was an airman working in a communication center we had the General come down and tried to get us to disobey the regs on security. Our Chief Master Sgt politely informed him, "Sir with all due respect, this is MY communication Center and we will NOT break the rules." You do not mess with a CMSgt. The General backed down and left.

This Soldier wants attention, not respect. Ignore her/him and they'll go away.

You should confront but do it one on one and away from others. Of course do it with the proper respect for the rank. In this case, if I were a female, I would start off with perhaps complimenting her on her lipstick color and then stating, “I’d love to wear it too, but I thought lipstick couldn’t conflict with skin tone per regulation?” Always better to respect rank AND ego if possible. However, if someone was blatantly breaking regulations and was causing a public nuisance then I would confront them in front of others. Of course any violation which has a safety or security concern should be corrected on the spot regardless of the difference in rank (just be sure it’s an obvious violation especially if you’re say a private and the violator is a senior rank). Without the discipline which the regulations instill, we are not an effective fighting force. It’s discipline that wins battles.

I am retired Army. I worked in Iraq for a while after I got out. One morning at breakfast a few soldiers sat at the table with me. While I was eating I noticed a Lieutenant had her name tape upside down. I simply got up, walked to her side of the table, bent down to whisper in her ear of the infraction. She thanked me then asked the people with her why the hell didn't any of them tell her she was jacked up.

Excellent response.

No one likes to be corrected in front of anyone. It's always best to use tact and to do so (if possible) away from others. If that's not possible, you should go to a higher ranking person and express your displeasure of seeing someone of a higher rank than you blatantly disregarding the regs.